US2901495A - Addition products of fatty acids and unsaturated nitro compounds - Google Patents
Addition products of fatty acids and unsaturated nitro compounds Download PDFInfo
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- US2901495A US2901495A US619909A US61990956A US2901495A US 2901495 A US2901495 A US 2901495A US 619909 A US619909 A US 619909A US 61990956 A US61990956 A US 61990956A US 2901495 A US2901495 A US 2901495A
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- Prior art keywords
- conjugated
- fatty acid
- acid
- adduct
- fatty acids
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 32
- 229930195729 fatty acid Natural products 0.000 title claims description 32
- 239000000194 fatty acid Substances 0.000 title claims description 32
- 150000004665 fatty acids Chemical class 0.000 title claims description 32
- 150000002828 nitro derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- JBYXPOFIGCOSSB-XBLVEGMJSA-N 9E,11E-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C\CCCCCCCC(O)=O JBYXPOFIGCOSSB-XBLVEGMJSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 6
- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-N 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 5
- 229940108924 conjugated linoleic acid Drugs 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- GKJZMAHZJGSBKD-UHFFFAOYSA-N (10E,12E)-Octadeca-9,11-dienoic acid Natural products CCCCCC=CC=CCCCCCCCCC(O)=O GKJZMAHZJGSBKD-UHFFFAOYSA-N 0.000 description 3
- GKJZMAHZJGSBKD-BLHCBFLLSA-N (10e,12e)-octadeca-10,12-dienoic acid Chemical compound CCCCC\C=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-BLHCBFLLSA-N 0.000 description 3
- GKJZMAHZJGSBKD-ANYPYVPJSA-N 10-trans-12-cis-linoleic acid Natural products CCCCCC=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-ANYPYVPJSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000001268 conjugating effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 1
- SYZVQXIUVGKCBJ-UHFFFAOYSA-N 1-ethenyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(C=C)=C1 SYZVQXIUVGKCBJ-UHFFFAOYSA-N 0.000 description 1
- JSPNBERPFLONRX-UHFFFAOYSA-N 1-methyl-4-(2-nitroethenyl)benzene Chemical compound CC1=CC=C(C=C[N+]([O-])=O)C=C1 JSPNBERPFLONRX-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- -1 nitroethyl Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/51—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
Definitions
- This invention relates to novel chemical compounds which have particular value as intermediates for the preparation of synthetic resins, plasticizers, and adhesives.
- the invention concerns addition products of nitroolefins and conjugated, long-chain poly-unsaturated fatty acids.
- the aforesaid addi tion products, or adducts as they may be termed are prepared by reaction of a nitroolefin with a long-chain, conjugated polyolefinic fatty acid.
- the reaction which takes place is illustrated by the equation below as specifically applied to fi-nitrostyrene and 9,11-octadecadienoic acid, by way of example.
- OH3(OH2)5-CHCH GHCH(CH2)TCOOH OH-OH l wherein one X is nitro (NO the other X is phenyl
- the reaction will proceed in analogous manner, the alpha and beta carbon atoms of the nitroolefin attaching to the end carbon atoms in the conjugating grouping.
- the products can be prepared from any compound in the category of long-chain, conjugated polyolefinic fatty acids.
- the critical feature in any case is the presence in the fatty acid of the conjugated system
- Preferred acids to be used in the process of the invention are 9,11-octadecadienoic acid and 10,12-octadecadienoic acid.
- Another preferred acid is conjugated linoleic acid which may be prepared in known manner from ordinary linoleic acid.
- Other suitable conjugated acids are those obtained by conjugating the fatty acids of soynited States Patent 0 bean oil, safiiower oil, sunflower oil, cottonseed oil, or other glyceride oil containing a high percentage of linoleic acid. Processes for producing conjugated fatty acids from such naturally-occurring fatty acids are well known in the art.
- the nitroolefin reactant may be any compound of the formula Where R is hydrogen or hydrocarbon.
- R may be alkyl, alkaryl, aryl, aralkyl or a cycloalkyl radical.
- Typical examples of such compounds are nitroethylene, lnitroprop'ylene, l-nitrobutene-l, l-nitropentene-l, 1-nitro-3-methyl-pentene-1, nitrohexene-l, l-nitroheptene-l, l-nitrooctene-l, SB-nitrostyrene, 1-nitro-2-paratolylethene, l-nitr -2-cyclohexylethene, l-nitro-Z-benzylethene, l-nitro-Z-(paraisopropylphenyl) ethene, and so forth.
- the process of the invention essentially involves contacting the nitroolefin with the conjugated fatty acid.
- the temperature of reaction is not critical. Usually the temperature is at least 50 C. so that the reaction will take place at a practicable rate. On the other hand, the upper limit of temperature should be about 200 C. to minimize polymerization of the conjugated fatty acid. In general, a temperature around -150 C. is preferred.
- the two reactants are usually used in equimolar proportions, although it is preferred to employ an excess of the nitroolefin to ensure complete reaction. To assist in getting maximum contact between the reactants, it is preferred to employ a solvent.
- solvents which may be used are benzene, toluene, xylene, chloroform, heptane, mixtures of petroleum hydrocarbons and the like. It is obvious that other inert, volatile organic solvents can be employed.
- the reaction time will, of course, vary depending on the nature of the conjugated fatty acid and particularly on temperature. In many cases at a temperature of about 130 C. C. the reaction will be complete in about 12-48 hours.
- the products of the invention are used for a wide variety of purposes.
- the products may be reduced to convert the nitro group to an amine group.
- the resulting amino acids maybe selfcondensed to yield polyamides.
- These polyamides are useful for example in producing protective coatings on surfaces, as adhesives for paper, cellophane and other plastic films, for producing laminated structural materials such as glass fiber laminates, as cross-linking agents for use with epoxy resins, etc.
- An illustration of such use of the compounds of the invention is given in Example 3 below.
- the amino acids they may be reacted with other polybasic carboxylic acids or polyamines to give useful polyamides having resinous charactertistics.
- Plasticize-rs can also be prepared by esterifying the carboxyl group of the nitroadduct and reducing the nitro group to an amino group which is then acylated. More vigorous reduction of the nitroadducts yields saturated amino alcohols which are of value as intermediates in the synthesis of polyamides, plasticizers and adhesives.
- Example 1 A benzene solution containing 1.6 moles of nitroethyl A benzene solution containing 1 mole of B-nitrostyrene and 9,11-octadecadienoic acid is heated in a sealed tube at 110 C. for 90 hours. Purification of the reaction mixture gives a 27 percent yield of a liquid having the following analysis: carbon, 72.72; hydrogen, 9.24. The theoretical analysis for the desired adduct is: carbon, 72.69; hydrogen, 9.15.
- Example 3 One and one-half grams of the product of Example 1 was dissolved in 30 ml. of ethanol. To this solution was added about 3 grams of Raney nickel catalyst and the mixture was subjected to hydrogen under a pressure of 40 lbs. per sq. in. The hydrogenation was conducted at room temperature for 1 hour. The resulting solution was filtered free from catalyst, concentrated and the saturated amino acid precipitated by addition of diethyl ether. The product was washed with diethyl ether and dried. The product obtained in a yield of 35 percent, had a melting point of 155-165 C., and was found to contain 4.04 percent nitrogen (theoretical 3.96 percent). The formula of the product is as follows:
- the saturated amino acid as described above is also suitable for preparing useful polymeric products in the manner as described in US. Patents Nos. 2,071,250, 2,071,253, and 2,440,516.
- An adduct of a long-chain, conjugated polyolefinic monocarboxylic fatty acid having at least 8 carbon atoms and a compound having the radical -CH CHNO 2.
- An adduct of a long-chain, conjugated diolefinic monocarboxylic fatty acid having at least 8 carbon atoms and a compound having the radical -CH CNO 11.
- An adduct of a long-chain, conjugated diolefim'c monocarboxylic fatty acid having at least 8 carbon atoms and beta-nitrostyrene is provided.
- the compound of claim is conjugated soybean fatty acid.
- fatty acid is a conjugated diolefinic fatty acid containing 18 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
ADDITION PRODUCTS OF FATTY ACIDS AND UNSATURATED NITRO COMPOUNDS No Drawing. Application November 1, 1956 Serial No. 619,909
21 Claims. (Cl. 260-404) (Granted under Title 35, US. Code (1952 see. 266) A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the world for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.
This invention relates to novel chemical compounds which have particular value as intermediates for the preparation of synthetic resins, plasticizers, and adhesives. In particular, the invention concerns addition products of nitroolefins and conjugated, long-chain poly-unsaturated fatty acids.
In accordance with the invention the aforesaid addi tion products, or adducts as they may be termed, are prepared by reaction of a nitroolefin with a long-chain, conjugated polyolefinic fatty acid. The reaction which takes place is illustrated by the equation below as specifically applied to fi-nitrostyrene and 9,11-octadecadienoic acid, by way of example.
OH3(OH2)5-CHCH=GHCH(CH2)TCOOH OH-OH l wherein one X is nitro (NO the other X is phenyl Where the fatty acid reactant is a different conjugated polyolefinic acid, the reaction will proceed in analogous manner, the alpha and beta carbon atoms of the nitroolefin attaching to the end carbon atoms in the conjugating grouping.
In general, the products of the invention derived from conjugated diolefinic acids may be described as compounds having at least 8 carbon atoms of the formula RCHCH=CH-CHR'-Cl 0H HC-CH- X 1'; wherein R is hydrogen or alkyl, R is al'kylene and one X is nitro, the other X is a member of the group consisting of hydrogen and hydrocarbon radicals.
The products can be prepared from any compound in the category of long-chain, conjugated polyolefinic fatty acids. The critical feature in any case is the presence in the fatty acid of the conjugated system Preferred acids to be used in the process of the invention are 9,11-octadecadienoic acid and 10,12-octadecadienoic acid. Another preferred acid is conjugated linoleic acid which may be prepared in known manner from ordinary linoleic acid. Other suitable conjugated acids are those obtained by conjugating the fatty acids of soynited States Patent 0 bean oil, safiiower oil, sunflower oil, cottonseed oil, or other glyceride oil containing a high percentage of linoleic acid. Processes for producing conjugated fatty acids from such naturally-occurring fatty acids are well known in the art.
The nitroolefin reactant may be any compound of the formula Where R is hydrogen or hydrocarbon. In the hydrocarbon category, R may be alkyl, alkaryl, aryl, aralkyl or a cycloalkyl radical. Typical examples of such compounds are nitroethylene, lnitroprop'ylene, l-nitrobutene-l, l-nitropentene-l, 1-nitro-3-methyl-pentene-1, nitrohexene-l, l-nitroheptene-l, l-nitrooctene-l, SB-nitrostyrene, 1-nitro-2-paratolylethene, l-nitr -2-cyclohexylethene, l-nitro-Z-benzylethene, l-nitro-Z-(paraisopropylphenyl) ethene, and so forth. These reactants can be generically referred to as nitrohydrocarbons which contain the radical CH:=CH-NO The process of the invention essentially involves contacting the nitroolefin with the conjugated fatty acid. The temperature of reaction is not critical. Usually the temperature is at least 50 C. so that the reaction will take place at a practicable rate. On the other hand, the upper limit of temperature should be about 200 C. to minimize polymerization of the conjugated fatty acid. In general, a temperature around -150 C. is preferred. The two reactants are usually used in equimolar proportions, although it is preferred to employ an excess of the nitroolefin to ensure complete reaction. To assist in getting maximum contact between the reactants, it is preferred to employ a solvent. Some of the solvents which may be used are benzene, toluene, xylene, chloroform, heptane, mixtures of petroleum hydrocarbons and the like. It is obvious that other inert, volatile organic solvents can be employed. To enable the use of a temperature above the boiling point of the solvent, it is preferred to maintain the reaction mixture of nitroolefin, diolefinic acid and solvent in a sealed vessel capable of resisting the resulting super-atmospheric pressure. The reaction time will, of course, vary depending on the nature of the conjugated fatty acid and particularly on temperature. In many cases at a temperature of about 130 C. C. the reaction will be complete in about 12-48 hours.
As noted above, the products of the invention are used for a wide variety of purposes. For example, the products may be reduced to convert the nitro group to an amine group. The resulting amino acids maybe selfcondensed to yield polyamides. These polyamides are useful for example in producing protective coatings on surfaces, as adhesives for paper, cellophane and other plastic films, for producing laminated structural materials such as glass fiber laminates, as cross-linking agents for use with epoxy resins, etc. An illustration of such use of the compounds of the invention is given in Example 3 below. Instead of self-condensing the amino acids they may be reacted with other polybasic carboxylic acids or polyamines to give useful polyamides having resinous charactertistics. Another application of the product of the invention involves esterification of the carboxyl group of the nitroadduct to yield nitroesters suitable for use as plasticizers. Plasticize-rs can also be prepared by esterifying the carboxyl group of the nitroadduct and reducing the nitro group to an amino group which is then acylated. More vigorous reduction of the nitroadducts yields saturated amino alcohols which are of value as intermediates in the synthesis of polyamides, plasticizers and adhesives.
The following examples illustrate the invention.
Example 1 A benzene solution containing 1.6 moles of nitroethyl A benzene solution containing 1 mole of B-nitrostyrene and 9,11-octadecadienoic acid is heated in a sealed tube at 110 C. for 90 hours. Purification of the reaction mixture gives a 27 percent yield of a liquid having the following analysis: carbon, 72.72; hydrogen, 9.24. The theoretical analysis for the desired adduct is: carbon, 72.69; hydrogen, 9.15.
Example 3 One and one-half grams of the product of Example 1 was dissolved in 30 ml. of ethanol. To this solution was added about 3 grams of Raney nickel catalyst and the mixture was subjected to hydrogen under a pressure of 40 lbs. per sq. in. The hydrogenation was conducted at room temperature for 1 hour. The resulting solution was filtered free from catalyst, concentrated and the saturated amino acid precipitated by addition of diethyl ether. The product was washed with diethyl ether and dried. The product obtained in a yield of 35 percent, had a melting point of 155-165 C., and was found to contain 4.04 percent nitrogen (theoretical 3.96 percent). The formula of the product is as follows:
CHOH
Y Y wherein one Y is amino (NH and the other is hydrogen.
A quantity of the above heated 40 minutes at 210 0.05 mm. to form a resin.
saturated amino acid was C. and under a pressure of Some of the resin was dissolved in tetrahydrofurane and the solution cast on a glass plate to form a resin coating. The coating was found to have a pencil hardness of 3H.
The saturated amino acid as described above is also suitable for preparing useful polymeric products in the manner as described in US. Patents Nos. 2,071,250, 2,071,253, and 2,440,516.
Having thus described the invention, we claim:
1. An adduct of a long-chain, conjugated polyolefinic monocarboxylic fatty acid having at least 8 carbon atoms and a compound having the radical -CH=CHNO 2. An adduct of beta-nitrostyrene and 9,11-octadecadienoic acid.
3. An adduct of beta-nitrostyrene and 10,12-octadecadienoic acid.
4. An adduct of beta-nitrostyrene and conjugated linoleic acid.
5. An adduct of beta-nitrostyrene and conjugated soybean fatty acids.
6. An adduct of nitroethylene and 9,11-octadecadienoic acid.
7. An adduct of nitroethyleneand 10,12-octadecadienoic acid.
8. An adduct of nitroethylene and conjugated linoleic acid. a
9. An adduct of nitroethylene and conjugated soybean fatty acids.
10. An adduct of a long-chain, conjugated diolefinic monocarboxylic fatty acid having at least 8 carbon atoms and a compound having the radical -CH=CNO 11. An adduct of a long-chain, conjugated diolefinic monocarboxylic fatty acid having at least 8 carbon atoms and nitroethylene.
12. An adduct of a long-chain, conjugated diolefim'c monocarboxylic fatty acid having at least 8 carbon atoms and beta-nitrostyrene.
13. The compound of claim 10 wherein the fatty acid is a conjugated octadecadienoic acid.
14. The compound of claim 10 wherein is conjugated linoleic acid.
15. The compound of claim is conjugated soybean fatty acid.
16. The process which comprises reacting a long-chain, conjugated polyolefinic monocarboxylic fatty acid having at least 8 carbon atoms with a compound having the radical CH=CHNO and recovering the resulting adduct.
17. The process which comprises reacting a long-chain, conjugated polyolefinic monocarboxylic fatty acid having at least 8 carbon atoms with nitroethylene and recovering the resulting adduct.
18. The process which comprises reacting a long-chain, conjugated polyolefinic monocarboxylic fatty acid having at least 8 carbon atoms with beta-nitrostyrene and recovering the resulting adduct.
19. The process of claim 16 wherein the fatty acid is a conjugated diolefinic fatty acid containing 18 carbon atoms.
20. The process of claim 16 wherein the fatty acid is conjugated linoleic acid.
21. The process of claim 16 wherein the fatty acid is conjugated soybean fatty acids.
the fatty acid 10 wherein the fatty acid References Cited in the file of this patent
Claims (2)
1. AN ADDUCT OF A LONG-CHAIN, CONJUGATED POLYOLEFINIC MONOCARBOXYLIC FATTY ACID HAVING AT LEAST 8 CARBON ATOMS AND A COMPOUND HAVING THE RADICAL-CH=CH-NO2.
16. THE PROCESS WHICH COMPRISES REACTING A LONG-CHAIN, CONJUGATED POLYOLEFINIC MONOCARBOXYLIC FATTY ACID HAVING AT LEAST 8 CARBON ATOMS WITH A COMOPOUND HAVING THE RADICAL -CH=CH-NO2 AND RECOVERING THE RESULTING ADDUCT.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US619909A US2901495A (en) | 1956-11-01 | 1956-11-01 | Addition products of fatty acids and unsaturated nitro compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US619909A US2901495A (en) | 1956-11-01 | 1956-11-01 | Addition products of fatty acids and unsaturated nitro compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2901495A true US2901495A (en) | 1959-08-25 |
Family
ID=24483820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US619909A Expired - Lifetime US2901495A (en) | 1956-11-01 | 1956-11-01 | Addition products of fatty acids and unsaturated nitro compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2901495A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5548049A (en) * | 1992-07-03 | 1996-08-20 | Chemishe Fabrik Stockhausen Gmbh | Copolymers of allyliminodiacetic acid with unsaturated carboxylic acids and their use as complexing agents, peroxide stabilizers, builders in washing and cleaning products and dispersing agents |
-
1956
- 1956-11-01 US US619909A patent/US2901495A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5548049A (en) * | 1992-07-03 | 1996-08-20 | Chemishe Fabrik Stockhausen Gmbh | Copolymers of allyliminodiacetic acid with unsaturated carboxylic acids and their use as complexing agents, peroxide stabilizers, builders in washing and cleaning products and dispersing agents |
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